Dehydropeptide compounds, their production and their medical use

Abstract

This invention relates to dehydropeptides containing a tryptophan moiety useful as tumour-resolving and/or histolytic medicaments. Also included in the invention are methods for the preparation of said dehydropeptides, compositions containing said dehydropeptides and methods for the use of said dehydropeptides and dehydropeptide compositions.

What is claimed is: 
     
       1. A compound which is a dehydropeptide of the formula ##STR6## or a salt thereof, in which R 1  denotes a hydrogen atom, an optionally substituted alkyl, alkenyl, aralkyl, aralkenyl aryl, alkoxy group or a heterocyclic ring,   R 2  denotes a phenyl radical which is optionally substituted by alkyl, aryl, alkoxy, hydroxyl, nitro, amino, acylamino or halogen,   R 3  and R 4  both denote a hydrogen atom, or together denote an additional bond between the two carbon atoms,   R 5  denotes a hydroxyl group or an optionally substituted alkoxy, aralkoxy or amino group and   n is 1 or 0, and in which, when R 3  and R 4  both denote a hydrogen atom, the centre of asymmetry C* at the substituent R 3  is in the racemate form, or in the D-form or L-form.     
     
     
       2. A compound according to claim 1, in which R 1  denotes a hydrogen atom, an alkyl group with 1 to 4 carbon atoms or a phenyl or benzyl radical,   R 2  denotes a phenyl radical which is optionally substituted by alkyl with 1 or 2 carbon atoms or halogen,   R 3  and R 4  both denote a hydrogen atom or together represent an additional bond between the two carbon atoms,   R 5  denotes a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, a benzyloxy or amino group and   n is 1 or 0.   
     
     
       3. A compound according to claim 1, in which R 1  denotes a methyl group,   R 2  denotes a phenyl radical,   R 3  and R 4  both denote a hydrogen atom or together represent an additional bond between the two carbon atoms,   R 5  denotes a hydroxyl group and   n is 1.   
     
     
       4. A compound according to claim 3, in which R 3  and R 4  both denote a hydrogen atom, in their racemic form and in their optically active form.   
     
     
       5. A pharmaceutical composition containing as an active ingredient 1 to 90% of a compound according to claim 1 in admixture with a solid, liquid or liquefied gaseous diluent. 
     
     
       6. A pharmaceutical composition of claim 5 in the form of a sterile or physiologically isotonic aqueous solution. 
     
     
       7. A composition according to claim 5 or 6 containing from 5 to 50% by weight of the said active ingredient. 
     
     
       8. A medicament in dosage unit form comprising a compound according to claim 1 in an inert pharmaceutical carrier. 
     
     
       9. A medicament of claim 8 in the form of tablets, pills, dragees, capsules, ampoules or suppositories. 
     
     
       10. A method of treating tissues to provide histolytic effect which comprises administering to warm-blooded animals a histolytically effective amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament. 
     
     
       11. A method according to claim 10 in which the active compound is administered in an amount of 2 to 40 mg per kg body weight per day. 
     
     
       12. A method according to claim 10 or 11 in which the active compound is administered parenterally. 
     
     
       13. A compound according to claim 1 which is N-Acetyl dehydrophenylalanyl-L-tryptophan. 
     
     
       14. A compound according to claim 1 which is N-Acetyl dehydrophenylalanyl-D-tryptophan. 
     
     
       15. A compound according to claim 1 which is N-Acetyl dehydrophenylalanyl-dehydrotryptophan.